Diarylmethylidenefuran derivatives and their uses in therapeutics
The present invention relates to the derivatives of the formula ##STR1## and to their use in therapeutics, especially as drugs with anti-inflammatory and analgesic properties.
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Claims
1. A diarylmethylidenefuran compound of formula (I): ##STR25## wherein: the rings A and B independently are:
- a phenyl radical,
- a naphthyl radical,
- a pyridyl radical,
- a furyl radical, or
- a thienyl radical;
- at least one of the substituents X.sub.1, X.sub.2, Y.sub.1 or Y.sub.2 is necessarily:
- an S(O).sub.n --R group, in which n is an integer equal to 0, 1 or 2 and R is a lower alkyl radical having 1 to 6 carbon atoms or a lower haloalkyl radical having 1 to 6 carbon atoms, or
- an SO.sub.2 NH.sub.2 group; and is located in the para position,
- the others independently being:
- a hydrogen atom,
- a halogen atom,
- a lower alkyl radical having 1 to 6 carbon atoms,
- a trifluoromethyl radical,
- a lower O-alkyl radical having 1 to 6 carbon atoms, and
- R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are:
- a hydrogen atom,
- a halogen atom,
- a lower alkyl radical having 1 to 6 carbon atoms,
- a lower haloalkyl radical having 1 to 6 carbon atoms,
- an aromatic radical selected from the group consisting of phenyl and naphthyl, or
- R.sub.1 R.sub.2 or R.sub.3 R.sub.4 are an oxygen atom, or
- R.sub.1,R.sub.2 or R.sub.3,R.sub.4, together with the carbon atom to which they are attached, form a saturated hydrocarbon ring having from 3 to 7 carbon atoms.
2. A compound of formula (I) according to claim 1, wherein:
- the rings A and B independently are:
- a phenyl radical,
- a naphthyl radical,
- a pyridyl radical,
- a furyl radical, or
- a thienyl radical;
- at least one of the substituents X.sub.1, X.sub.2, Y.sub.1 or Y.sub.2 is necessarily SCH.sub.3, SO.sub.2 CH.sub.3 or SO.sub.2 NH.sub.2 group,
- the others independently being:
- a hydrogen atom,
- a halogen atom,
- a lower alkyl radical having 1 to 6 carbon atoms,
- a trifluoromethyl radical, or
- a lower O-alkyl radical having 1 to 6 carbon atoms;
- R.sub.1 R.sub.2 are an oxygen atom; and
- R.sub.3 R.sub.4 independently are a hydrogen atom or a lower alkyl radical having 1 to 6 carbons.
3. A compound according to claim 1, wherein the ring B is a phenyl radical.
4. A compound according to claim 1, wherein the ring A is a phenyl radical or a pyridyl radical.
5. A compound according to claim 1, wherein X.sub.1 is a 4-SO.sub.2 CH.sub.3 group or a 4-SO.sub.2 NH.sub.2 group, and X.sub.2 is a hydrogen atom.
6. A compound according to claim 1, wherein Y.sub.1 is a fluorine atom, a chlorine atom or a methyl radical, and Y.sub.2 is a hydrogen atom, a fluorine atom or a chlorine atom.
7. A compound according to claim 1, wherein R.sub.1 R.sub.2 are an oxygen atom and R.sub.3 and R.sub.4 are each a hydrogen atom.
8. A compound according to claim 1, which is selected from the following compounds: ##STR26##
9. A compound according to claim 1, and having the formula ##STR27##
10. A compound according to claim 1, and having the formula ##STR28##
11. A pharmaceutical composition, which comprises a pharmaceutically effective amount of a compound of formula (I) as defined in claim 1, incorporated in a pharmaceutically acceptable excipient, vehicle or carrier.
12. A pharmaceutical composition with anti-inflammatory and analgesic activity, which contains a pharmaceutically effective amount of a compound of formula (I) as defined in claim 1, incorporated in a pharmaceutically acceptable excipient, vehicle or carrier.
13. A pharmaceutical composition according to claim 11, which is in the form of gelatin capsules or tablets containing a dose of 1 mg to 1000 mg.
14. A pharmaceutical composition according to claim 11, which is in the form of injectable preparations containing a dose of 0.1 mg to 500 mg.
15. A method for treating inflammation in a mammal which comprises administering an anti-inflammatory effective amount of a compound of formula I as defined in claim 1 to said mammal.
16. A method for treating pain in a mammal which comprises administering an effective amount of a compound of formula I as defined in claim 1 to said mammal.
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Type: Grant
Filed: Mar 27, 1997
Date of Patent: Sep 15, 1998
Assignee: Laboratories UPSA (Agen)
Inventors: Eric Nicolai (Rueil Malmaison), Jean-Marie Teulon (La Celle Saint Cloud)
Primary Examiner: Jane Fan
Attorney: Barry J. Marenberg
Application Number: 8/825,242
International Classification: C07D40506; A61K 5144;